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Wednesday night on Annapolis waters

Four distinguished-looking gentlemen in fine blue blazers with race committee patches fire cannons from the second deck of the Annapolis Yacht Club.

Four distinguished-looking gentlemen in fine blue blazers with race committee patches fire cannons from the second deck of the Annapolis Yacht Club. An attractive young professional woman, expertly outfitted in sailing attire and carrying a Musto backpack, races down the dock to meet the boat before it departs. Slack-tied businessmen and their dates jockey for the best tables in the bar of the Chart House and on the outdoor patio of Carrol’s Creek Cafe to catch the beauty and grace of large sailboats racing into AnnapolisHarbor at sunset.

These are the sights and scenes that play out weekly from early May through late August while the Annapolis Yacht Club Wednesday Night Racing series is being held. It has become an Annapolis tradition like no other, and after nearly 50 years it has developed its own habits and rituals.

“It doesn’t matter what is going on at work or other aspects of my life, I know that come 5 o’clock on Wednesday night I’ll be climbing aboard this boat to go out sailing,” says Steve Siska, who has been crewing on the J/30 Cannonball for nearly 25 years.

Siska, an insurance salesman, had zero sailing experience before being pressed into service by Dr. William Wallop, a longtime resident of Winchester-on-the-Severn. Brothers Doug and Billy Wallop routinely recruited the neighborhood on behalf of their father, and as a result many of their friends have become regular members of the crew.

These days Doug Wallop skippers the boat, and crew often consists of close friends such as Lou Stevens, Earl Chambers, Brian Lease, Ralph Riddle and Dave Eckels. Siska has risen the ranks to the point he now serves as tactician aboard Cannonball.

“That is what I absolutely love the most about Wednesday night: I get to spend a few hours sailing with my best buddies in the world,” says Doug Wallop, a physical therapist who now lives on KentIsland. “Our boat has always been raced by friends and family. It’s as much about spending quality time together and catching up with everyone’s lives as it is about winning a race.”

Wednesday night racing was the brainchild of Gaither Scott, past commodore and longtime race committee chairman for Annapolis Yacht Club. Mr. Scott introduced the idea to Annapolis in 1959 after seeing weeknight racing at East Greenwich Yacht Club in Rhode Island. Annapolis Yacht Club’s inaugural series featured no race committee, no prizes and no scoring, but there was a picnic supper after racing. Herreshoff 23-footers, 5.5 meters, Bermuda One Designs and Rainbows comprised the early classes, but interest waned in the mid 1960s. To increase participation, smaller classes of boats were invited, and entries increased to 112 boats by 1967.

By the 1980s the Wednesday Night Races had grown so popular that the Coast Guard had to limit entries to 150 boats for safety reasons. That is due largely to the unique nature of the series, which brings the fleet through the heart of Spa Creek to a finish line set directly in front of the Annapolis Yacht Club. Making the final approach to the finish both interesting and dicey is the fact the raceboats must weave through the myriad boats moored in the creek. Over the years there have been a handful of incidents involving collisions or near misses between racing and moored boats.

Annapolis Yacht Club is near full capacity this year with 145 boats entered, although not all show up at the start line every Wednesday night. Organizers have divided the series into three parts so skippers can take vacations without worrying about missing races and thus hurting their overall score. Bobby Frey, current chairman of the AYC special events committee, says the Wednesday Night Races have increasingly become the primary competitive outlet for many boat owners.

“With people’s schedules these days, devoting an entire Saturday and Sunday to a weekend regatta is not as feasible,” says Frey. “As a result, Wednesday Night has evolved into the No. 1 racing venue for many folks because it’s quicker and easier. What used to be a casual beer can regatta has suddenly grown more serious, and that has changed the overall dynamic.”

Frey has taken great pains to professionalize the Annapolis Yacht Club race committee because competitive skippers simply won’t stand for mistakes. The club has 25 different courses it can use for the Wednesday Night series, and it’s important to choose the correct one based on wind velocity and direction. All races start in the middle of the Severn River off Trident Point and take the fleet into Chesapeake Bay. Courses are eight to 10 nautical miles in length and take just under two hours to complete.

Despite the increased level of competitiveness, the Wednesday Night Races retain a casual atmosphere that is centered around friendships. Todd Hiller and Peter McChesney, longtime rivals in the J/22 Class, have joined forces to sail a J/105 on Wednesday night. That ensures that a quality skipper will race the boat if either partner cannot make it one week. There was some good-natured ribbing a few Wednesdays ago, when Hiller won the race while McChesney was attending his son’s Little League baseball game.

Both men routinely take their young children out on the J/105, Kokopelli, so they can learn the basics of sailing. “Having my son sit beside me while I steered the boat was a moment I could not wait to come,” says Hiller, who had a creative way to keep 5-year-old Andrew interested out on the course. “I told Andrew that we were a pirate ship and that we had to beat all the other pirates back to port in order to win the treasure.”

What happens on the water is just one element of the Wednesday night experience. Socializing at the yacht club afterward over food and refreshments is the other half of the equation. Many teams tie up at the dock, then sit in the cockpit to converse before heading up to the post-race party on the veranda at the club. Others head across the SpaCreekBridge to the Boatyard Bar & Grill, where the owner plays videotape highlights of that night’s action on a big-screen television.

Up on the second deck of Annapolis Yacht Club, the four men in blue blazers are recording finishes while giving the gun to the first boat to cross the line in each class. An outdoor table on the patio is a coveted spot on Wednesday night, as patrons can enjoy dinner while watching the sailboats come into the harbor.

Longtime race committee member Dan Spadone is using an air horn to sound the start for the Herreshoff fleet, and that has annoyed a longtime observer and yacht club member. “Enough of that wimpy horn. Get the cannon back out,” the man bellows.

It turns out the cannon that blasted whenever the winning boat came across the line has been retired for the time being due to an anonymous complaint. Club officials are investigating whether the disturbance warrants not using the cannon.

Yet that cannon is part of the Wednesday night racing scene that most people in Annapolis enjoy. It has gotten to the point that restaurants such as Carrol’s Creek and Chart House have come to rely on the increased business the summer races generate.

“Wednesday night racing in Annapolis is an event, an overall experience. There are people who come downtown just to stand on the bridge or sit at Carroll’s Creek, and they expect to see the races,” says Frey. “In a way, we have an obligation to finish the races inside the harbor because so many businesses benefit from the fact that those sailboats come racing past like clockwork every Wednesday night. That is what this series has come to mean to our town.”

However, most of the top J/22 and J/24 sailors prefer the Thursday Night Series out of J/World Annapolis because the fleets are bigger and the competition is tougher. Former J/World Performance Sailing School director Jahn Tihansky founded the series back in 1990, and it now attracts 20 to 25 J/22s and J/24s per week.

“We have a different format than Wednesday night. We run short windward-leeward courses and try to get in at least three races per night,” says Dan Wittig, co-director of the Thursday Night Series for J/World Annapolis. “It’s more analogous to the one-design racing they do on weekends.”

Courses are usually set on the Severn River just off ChesapeakeHarbor, and the season consists of two 10-race series. Entry fee provides for a keg of beer back at J/World, and the J/24 skippers now conduct a rules discussion after racing.

“Our series is relaxed yet competitive,” says Wittig. “We have top-notch skippers who really go after each other out on the race course, but I don’t think anyone really ultimately cares who wins the series.”